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Nucleosteroids: Synthesis of purinyl-steroid derivatives under mitsunobu reaction conditions

✍ Scribed by Raúl A. Cadenas; María E. Gelpi; Jorge Mosettig

Publisher
Journal of Heterocyclic Chemistry
Year
2005
Tongue
English
Weight
38 KB
Volume
42
Category
Article
ISSN
0022-152X

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✦ Synopsis

The feasibility of using the Mitsunobu reaction for coupling of purines with steroids to obtain nucleosteroids was investigated in the particular case of 6-chloropurine and cholesterol. Three principal products were obtained: 3β-(6-chloropurin-9-yl)-5-cholestene (1), 3α-(6-chloropurin-9-yl)-5cholestene (2), and 6β-(6-chloropurin-9-yl)-3,5-cyclocholestane (3), isolated with 10.5%, 22.7%, and 12.6% yield, respectively. The stereochemical and structural diversity of the coupling products are explained by the formation of a homoallylic carbocation through participation of the double bond of cholesterol.

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